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After a successful conquest of the Kingdom of Portugal, Philip II of Spain was confronted with a new conflict with António, Prior of Crato, forcing him to delay his acclamation and recognition of Prince Diogo, his son, as heir and legitimate successor to the Portuguese Crown.

Philip had opened the Junta dos Estados (English: Council of State) on 17 April 1581, with the objective of establishing guarantees to the Portuguese Crown, and in order to facilitate this he published an amnesty for those implicated in supporting the Prior of Crato, during the succession crisis. But, it was not a general amnesty and contained many artificial clauses, that the King refused to alter, and who refused to pardon many, including António, the Count of Vimioso, the Bishop of Guarda (son of the Count), as well as 52 others.

When he eventually arrived in Almada, the King was advised of the bad disposition that existed on the island of Terceira towards his reign, and that they had refused to accept Ambrósio de Aguiar Coutinho as the new governor. Consequently, he ordered the preparation of an armada that could potentially secure the island of São Miguel, place locals under the obedience of the Crown, and facilitate shipping to the Indies. The fleet, under the command of Pedro de Valdez, was ordered to take Terceira until greater forces could be sent to assist the control the Azores. With Pedro, Phillip sent letters for the government in Angra do Heroísmo and particular instructions for the residents of the island, that with peace the new restrictions would be alleviated.

From his base on the island of Santa Maria, Pedro de Valdez awaited the arrival of reinforcements from the continent, where he trained his crews, and continued repairs on the fleet. By spring he left Santa Maria with seven large carracks and 1000 troops. His small armada arrived in São Miguel where he took on provisions that were supplied by Governor Ambrósio de Aguiar Coutinho, and his cousin, Juan de Valdez, who was a knight/horseman joined the fleet. The group included eight galleons, one patache and a fire-ship, that was there initially to observe; it was with this detachment that they embarked for Terceira.

On the morning of 5 July 1581 the armada appeared along the horizon, visible from the Bay of Angra to the east. There was mixed reaction in the populace on the fleets arrival, as the island's residents were equally divided between the two factions. Some believed the fleet to be António's supporters from France (he had petitioned Catherine de Medici for help) and England, with much promised aid, while the remaining nobles hoped that it brought Philip II's armies to subjugate the island and put an end to António's reign. His supporters, confident in support from their allies, were not as vigilant as the ships appeared on the horizon; their hopes of triumph and confidence in their cause blinded them to the true nature of the fleet, and they were not prepared for an attack.

This immediately changed as the ships crossed in front of the port and began to shell the city and the ships in the harbour. At the time, the fortress of Santo António did not exist, and troops from the ships disembarked the next morning near Monte Brasil, confiscated a fishing boat that could have been used to alert the local residents, and strengthened their positions overlooking the city by the third night. The commander, Valdez sent a dispatch to Governor Ciprião de Figueiredo e Vasconcelos and the rest of the landed gentry, instructing them to surrender in the name of King Philip II, and advising them that monarch was willing to pardon them for their rebellion and provide them with other favours with the King's peace. Valdez finally noted that should they refuse, he was ready to send 1,000 troops to take the island, without providing quarter to anyone.

Most islanders reacted belligerently towards the Castilian, seeing the threats of force and favourable promises as nothing more than bluster. Terceirenses, although small in number, were not interested in reconciliation with Lisbon, unless their patron António was willing to accept them. António was popular with the island residents, who embraced him as their sovereign and swore fealty. This reaction, although expected, also indicated the degree of support of rural islanders, and he was forced to wait in Angra Bay for news from Philip II.

Philip II of Spain heard of the state of Terceira and its dependants, and, except for São Miguel and Santa Maria, its residents rejected the installation of the new Governor that he sent to the islands.

Without losing any time he prepared and armed a few ships necessary to conquer the rebel islands, under the command of Lopo do Figueiroa, in order to join Pedro Valdez's small flotilla. When Pedro heard that Lopo was on his way and, more importantly, had become the commander of the fleet, charged with conquering the renegade islands, he was incensed. Motivated by ambition, a potential victory and the glory associated with it, Pedro Valdez decided to disembark his forces in a pasture used by some of his troops to collect fruit or parlay with the local Portuguese. Valdez believed that the following tactic would end the rebellion: dispatch troops to join some of his men on the mainland, take Angra and refortify the enclave until Lopo de Figueiroa arrived to support (which was expected). He gave orders and prepared for the surprise attack for the following day.

The islanders had constructed posts along the coast to watch for enemy attacks; these posts were guarded by elements of the local militia and, in some cases, cannon. Consequently, on the morning of 24 July, Governor Ciprião do Figueiredo determined that the enemy, because of a few movements, intended to create a beachhead in the parish of Santo António do Porto Judeu. He ordered a contingent of the militia under Domingos Onsel to rendezvous in the area with 10 pikemen and 20 musket-armed infantrymen and to melt into the local population. In addition, the group was charged with defending the port and coast at the Casa da Salga, an area frequented by many of the Castilians in the days before the attack.

Onsel and his militia marched from Angra with a well-armed, munitioned group, and arrogantly believed his superiority to the unprepared Spanish. As a result, after arriving at Port Judeu, realizing that the local population and coastal defences were adequate, he dismissed his 10 pikemen and ordered them to return to Angra. Fearful of the consequences, the Governor sent to Port Judeu a second contingent that included a few infantrymen and horsemen along with the nobles Martim Simão de Faria, António de Ornelas Gusmão, Manuel Pires Teixeira, Manuel Gonçalves Salvago, ou Salgado, Pantaleão Toledo, Domingos Fernandes, and André Fernandes de Seia. The group, in counsel with Domingos Onsel, deliberated that their best option was to divide into smaller groups and stake out points along the coast, with some armed soldiers and members of the local population. Each team dispersed into an area of about a league, from Port Judeu's fort to Salga Bay, an act that dispersed their forces considerably.

On the morning of the feast day of Santiago (25 July), finding the waters peaceful and wind favourable, Pedro de Valdez ordered troops to set out on small launches and the seized boat, with his first column of 200 well-armed men some artillery. Pedro de Valdez's plan was to disembark his men at Casa da Salga, in the valley of Porto Judeu (a mile from Vila de São Sebastião). As he recognized, Salga Bay was a relatively large bay with a deep channel that allowed easy offloading of men and munitions, and which extended inwards along the valley into a vast plain that reached towards Pico de Garcia Ramos (at the parish's northern limits).

In the early hours, the lookout sounded the alarm from Ponta dos Coelhos to warn that the enemy was drawing near. The bell was rung by Vicar Pereira in the bell-tower of the parochial church of Santo António to awaken the residents to the Spanish intervention. Domingos Onsel and his troops quickly reformed, but arrived too late to impede the Spanish landing at Port Judeu. Finding no resistance, and led by João de Valdez, the Spanish offloaded their artillery and men, including Juan de Bazan (nephew of the Marquese of Santa Cruz), the nephew of the Count of Alba, and many other experienced men, advanced into the valley, while 50 men remained behind to defend the beachhead.

As the battle progressed, a small group of local defenders captained by Baltasar Afonso Leonardes arrived in the valley and joined the battle. Meanwhile from Valdez's carracks another 200 men and arms had offloaded, so that "from daylight there could be on land 400 men, illustrious people, and old soldiers, who surely was fearful; and its order and force exemplified grande soldiers."

The Spanish forces expanded into the plain of Vale, while the defenders gathered in the high ground near a spring and manor owned by the farmer Bartolomeu Lourenço, his wife Brianda Pereira (a nobleman's daughter), and their children. Brianda was the object of Spanish attention, and the family home was the first conquest of the battle: her husband was gravely wounded along with one of his sons during the defence, but nonetheless arrested by the advancing Spanish, as she escaped. The family home was sacked, destroyed and the wheat store was ransacked. But unfortunately for the Spanish, she was able to motivate and exhort the women in the nearby villages to stand alongside their men in the defence of the island.

By this time, Pedro de Valdez had finally made it to shore, with the rest of his 1,000 troops and made camp at the beachhead.

At about 9:00 in the morning reinforcements arrived from Angra under the command of Sebastião do Canto, Pedro Cota da Malha, Bernardo de Távora, Gaspar Cavio de Barroso and Francisco Dias Santiago; from Praia contingents under Gaspar Camelo do Rego and Simão de Andrade Machado; from Vila de São Sebastião Baltasar Afonso (as the Captain-major in the jurisdiction) and André Gato (captain of the forces in Porto Judeu); a contingent of French troops onboard António Eschalim's carrack; and many other people that swelled their ranks to 6,000 combatants. This group slowly advanced on the Spanish in the plain and towards the coast. Captain Artur de Azevedo de Andrade arrived with an artillery piece, marching along the coast toward the beachhead, intent on creating confusion in the Spanish ranks, but was attacked and shamefully retreated. The Spanish dragged the cannon to their camp, and began singing songs of victory, secure in the belief that they had the advantage, protected the beachhead and ensured the safety of the armada.

By midday, the Spanish on the coast had not seen any Portuguese soldiers and believed their leaders to be arrested or hiding in the mountains, or that the islanders had realized the folly and inevitable losses from Valdez's 1,000 troops. This quickly changed as the Portuguese arrived within sight of the beach, forcing Valdez to escape to his ship.